Polymers with photographically useful groups can be used in many applications. In comparison with ordinary photographically useful compound, polymers with photographically useful groups offer the advantage of allowing a range of physical properties. Their solubility, absorption, migration, and viscosity are tunable. They do not sublime, are non-abrasive, and generally have low toxicity. Moreover, introduction of some special groups to the polymer may add value to special applications. Examples of specific applications for polymers containing photographically useful groups include photographic materials (including photographic films and papers), photographic processing medium, optical data storage, diagnostic testing, printing, microlithography, bulk coloration of polymer, ink jet, sensor, and the like.
The photographically useful groups can be obtained by incorporating monomer(s) or reactive compound(s) containing photographically useful group into polymer backbone or side chain through condensation polymerization, radical polymerization, or post modification. Linear and grafting types of polymer containing photographically useful groups with uncontrolled and simple macromolecular structure are known. For example, U.S. Pat. No. 4,340,664 discloses polymer latexes suited for homogeneously incorporating compounds with a photographically useful group into photographic silver halide emulsion materials. The latex incorporates a copolymer comprising a monomer with photographically useful group and an active monomer. U.S. Pat. Nos. 4,267,306, 4,359,570, and 4,617,373 disclose the preparation of colored polyester using copolymerized anthraquinone colorants. U.S. Pat. No. 4,477,635 discloses a process for preparing solvent soluble nonextractable aminotriarylmethane dye containing polyester, polycarbonate, polyurethane, and polyethyleneimine. U.S. Pat. No. 4,732,570 discloses colored thermoplastic resin composition which are provided by reacting a thermoplastic resin and a colorant in the form of an alkyleneoxy-substituted chromophore group. U.S. Pat. No. 5,188,641 discloses a process for preparing colored polymer by copolymerizing azo dye which contains at least one polymerizable unsaturated group. Copolymerization of azo or anthraquinone dyes containing olefinic groups with other vinyl monomers is disclosed in UK Pat. No. 877,402. U.S. Pat. No. 5,637,637 discloses a process of preparing waterborne copolymeric colorant via emulsion polymerization of an alkaline solution of a reactive dye and a vinyl monomer.
U.S. Pat. No. 5,098,475 discloses the preparation of dendrimeric dye or dyes by reacting Dow's STARBURST.TM. dendrimer with dye and use of such dye or dyes in ink formulations. Compared with linear and grafting polymers, dendritic polymers (or dendrimers) provide some unique advantages (Frechet, et al. Science, 269, 1080, 1995). First, the intrinsic viscosity of dendrimer is lower compared with linear analog with the same molecular weight. Second, the level of interaction between solvent and polymer is decreased and polymer becomes much more compact. Third, if the functional groups are located at the end of dendrimer, the functional group becomes more accessible and occupies much higher surface area. Since regularly branched dendrimers are typically prepared through lengthy multi-step syntheses, however, their availability is limited to a small group of functional monomers and industrial production of dendrimers is therefore limited.
The synthesis of hyperbranched polymers has also been recently disclosed. Hyperbranched polymers made by condensation reactions, e.g., have been suggested (Kim, et al., J. Am. Chem. Soc., 112, 4592 (1990); Hawker, et al. ibid, 113, 4583 (1991)), and synthesis of hyperbranched homopolymer via living chain polymerization process of vinyl monomers is disclosed by Frechet et al (Frechet, et al. Science, 269, 1080 (1995), U.S. Pat. Nos. 5,587,441, and 5,587,446, the disclosures of which are incorporated by reference herein in their entireties). Compared to dendrimer, hyperbranched polymers are less regular, but still may approximate at least some of the desirable properties of dendrimers (Frechet et al. J. Macromol. Sci., Pure Appl. Chem. A33, 1399 (1996)). More importantly, hyperbranched polymers are more conducive to industrial applications, especially those prepared via living chain polymerization processes.
Since their discovery, various vinyl hyperbranched polymers have been prepared by living cationic polymerization (Frechet, U.S. Pat. No. 5,587,441), atom transfer radical polymerization (Wang, et al., WO 9630421 A1), group transfer polymerization (Muller, et al., Polymer Preprint, 38(1), 498 (1997)), and stable radical polymerization (Hawker, et al., J. Am. Chem. Soc. 113, 4583 (1991)). Vinyl hyperbranched polymers with different structures, such as random copolymer (Gaynor, et al, Macromolecules, 29, 1079 (1996)), grafted hyperbranched copolymer (commonly assigned, copending U.S. Ser. No. 09/105,767, ), and block hyperbranched copolymer (commonly assigned, copending U.S. Ser. No. 09/105,765), can be made by the above processes. The resultant vinyl hyperbranched polymers from living chain polymerization comprise a totally different class of materials from the above-mentioned Dow dendrimer and its derivatives in terms of both chemical composition and macromolecular architecture.
None of the prior art discloses hyperbranched polymer ended with photographically useful group. Further, none of the prior art discloses vinyl hyperbranched polymer ended with photographically useful group.